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1
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0009696995
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Marcel Dekker: New York
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(a) Glycochemistry: Principles, Synthesis, and Applications; Wang, P. G., Bertozzi, C. P., Eds.; Marcel Dekker: New York, 2001; pp 425-492.
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(2001)
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Wang, P.G.1
Bertozzi, C.P.2
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0141601984
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(b) For a recent review on the synthesis of glycosaminoglycans, see: Yeung, B. K. S.; Chong, P. Y. C.; Petillo, P. A. J. Carbohydr. Chem. 2002, 21, 799-865.
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Yeung, B.K.S.1
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(a) For a review on the use of thioglycosides as glycosyl donors, see: Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205.
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Garegg, P.J.1
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5
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The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
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Tetrahedron Lett.
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Nakano, T.1
Ito, Y.2
Ogawa, T.3
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6
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0027641586
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The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
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Carbohydr. Res.
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Nilsson, M.1
Svahn, C.-M.2
Westman, J.3
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7
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0026713471
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The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
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Tetrahedron Lett.
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, pp. 5099-5102
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Goto, F.1
Ogawa, T.2
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8
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The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
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Garegg, P.J.1
Olsson, L.2
Oscarson, S.3
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9
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0031021254
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The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
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Tetrahedron Lett.
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Magaud, D.1
Grandjean, C.2
Doutheau, A.3
Anker, D.4
Shevchik, V.5
Cotte-Pattat, N.6
Robert-Baudouy, J.7
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10
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The few methods known in the literature are mainly based on the use of chromium-based oxidants: (a) Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1990, 31, 1597-1600. (b) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172. (c) Goto, F.; Ogawa, T. Tetrahedron Lett. 1993, 33, 5099-5102. (d) Garegg, P. J., Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200-2204. (e) Magaud, D.; Grandjean, C.; Doutheau, A.; Anker, D.; Shevchik, V.; Cotte-Pattat, N.; Robert-Baudouy, J. Tetrahedron Lett. 1997, 38, 241-244. (f) Allanson, N. M.; Liu, D.; Chi, F.; Jain, R. K.; Chen, A.; Ghosh, M.; Hong, L.; Sofia, M. J. Tetrahedron Lett. 1998, 39, 1889-1892.
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Tetrahedron Lett.
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Allanson, N.M.1
Liu, D.2
Chi, F.3
Jain, R.K.4
Chen, A.5
Ghosh, M.6
Hong, L.7
Sofia, M.J.8
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19
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0033534598
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See also ref 9
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Use of high concentrations of water and 2 equiv of BAIB facilitates the conversion of the aldehyde into the respective carboxylic acid: Epp, J. B.; Widlanski, T. S. J. Org. Chem. 1999, 64, 293-295. See also ref 9.
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J. Org. Chem.
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Epp, J.B.1
Widlanski, T.S.2
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21
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3142780644
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note
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Activation of the donor for 5 min at -60°C revealed incomplete activation of the donor glycoside. We therefore started the activation at -60°C and gradually warmed the reaction mixture to -40°C within 15 min (see also ref 7).
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22
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0029320055
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(a) Iwahara, S.; Suemori, N.; Ramli, N.; Takegawa, K. Biosci. Biotech. Biochem. 1995, 59, 1082-1085.
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0026500323
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0035122651
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Crich, D.; Smith, M.; Yao, Q.; Picione, J. Synthesis 2001, 323-326.
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Synthesis
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Crich, D.1
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25
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3142751202
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note
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2, p-TsOH, acetone; (2) TBDMSC1, imidazole, DCM, 0°C; (3) BzCl, pyridine, 0°C; and (4) TBAF, AcOH in THF (62% over four steps).
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